I went on a small hunting trip to West Elizabeth in search of a legendary animal, even though I have a $300 bounty on my head there from a previous story mission. The bounty hunters I previously encountered weren't that bad, so I thought I'd take the risk.
Turns out the bounty hunters get a bit meaner and more plentiful at these bounty levels, and the encounter didn't turn out well for me.
I'm wondering if I should just pay the bounty now, as the bounty hunter activity is quite annoying at that level and interferes with any activities I want to do in that area. But if there are other ways to reduce or eliminate bounties, or if they get cleared in the story or something like that, it would be quite a waste to pay it now. And right now $300 is a significant chunk of my total possessions.